Dimethylformamide → Pazinaclone

HRID 868252Notes

Reaction equation

HRID 868252 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]3[CH2:22][C:23](O)=[O:24])=[N:9]2)=[CH:4][CH:3]=1.CN(C)C=O.C(N(CC)CC)C.[O:38]1[C:42]2([CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[O:41][CH2:40][CH2:39]1>O>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:13]([CH2:22][C:23]([N:45]4[CH2:46][CH2:47][C:42]5([O:41][CH2:40][CH2:39][O:38]5)[CH2:43][CH2:44]4)=[O:24])[C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:20]3=[O:21])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 13655948HCID 13655948, compound

Product 1

HCID 59743PazinacloneYield 98.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 20.4 g of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindoline-1-acetic acid and 250 ml of dimethylformamide were added 16 ml of triethylamine, 10.4 g of 1,4-dioxa-8-azaspiro[4.5]decane and 16 ml of diethyl phosphorocyanide, and the mixture was stirred for 20 minutes. After addition of water, the resulting crystalline precipitate was collected by filtration, washed with water and dried to give 26.4 g of crude crystals. Recrystallization from methylene chloride-ethyl acetate gave 27.1 g of colorless crystals melting at 238°-239° C.

Workup

  1. filtrationthe resulting crystalline precipitate was collected by filtration
  2. washwashed with water
  3. customdried
  4. customto give 26.4 g of crude crystals
  5. customRecrystallization from methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-b62b9814afeb49a582129a343136ff1f
Source dataset
uspto-grants-1988_10
Patent number
US04778801

Reaction notes

Loading…